(Diethylamino)sulfur trifluoride → HCID 57658002, compound

HRID 1670846Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([N:31]3[CH2:36][CH2:35][CH:34]([C:37]([F:40])([F:39])[F:38])[CH2:33][CH2:32]3)=[O:30])=[CH:25][CH:24]=2)[CH:5]=[C:6]([Cl:22])[C:7]=1[CH2:8][N:9]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][CH:17](O)[CH2:16][CH2:15]2)[C:10]1=[O:21].C(N(S(F)(F)[F:47])CC)C>C(Cl)Cl.C(OCC)(=O)C>[Cl:22][C:6]1[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([N:31]3[CH2:32][CH2:33][CH:34]([C:37]([F:38])([F:39])[F:40])[CH2:35][CH2:36]3)=[O:30])=[CH:25][CH:24]=2)[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][N:9]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:15][CH2:16][CH:17]([F:47])[CH2:18][CH2:19]2)[C:10]1=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

Treat a 0° C. solution of 1-[3,5-dichloro-4′-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-3-(4-hydroxy-piperidin-1-yl)-pyrrolidin-2-one (0.090 g, 0.15 mmol) in CH2Cl2 (5 mL) with (diethylamino)sulfur trifluoride (0.049 g, 0.305 mmol) and stir for 1 hour at 0° C. under N2. Quench the reaction with saturated NaHCO3, dilute with ethyl acetate, and wash with water. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with a 0 to 10% methanol in CH2Cl2 gradient to afford 0.019 g (85%) of the titled product. Rf=0.56 (9/1 CH2Cl2/methanol). ES MS (m/z): 600 (M+).

Workup

customQuench
customthe reaction with saturated NaHCO3
washwash with water
dry with materialDry the organic layer (Na2SO4)
customremove the solvent in vacuo
customto afford crude product
custompurify with a 0 to 10% methanol in CH2Cl2 gradient

Sources & evidence

ORD record: ord-9c9235834bc8446189342fd7f6aa2c37
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994176B2

Reaction notes

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